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Synthesis 2004(9): 1527-1531
DOI: 10.1055/s-2004-822393
DOI: 10.1055/s-2004-822393
PAPER
© Georg Thieme Verlag Stuttgart · New York
Copper-Mediated Simple and Efficient Synthesis of Tribenzohexadehydro[12]annulene and Its Derivatives
Further Information
Received
4 May 2004
Publication Date:
26 May 2004 (online)
Publication History
Publication Date:
26 May 2004 (online)
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Abstract
A simple and efficient synthesis of tribenzohexadehydro[12]annulene and its derivatives was carried out using coupling reaction of acetylenes with iodoarenes in the presence of catalytic amounts of CuI and PPh3, together with three equivalents of K2CO3 in DMF. This synthetic procedure was applied to the synthesis of a large annulenoannulene derivative.
Key words
annulenes - cross-coupling - cyclizations - macrocycles - oligomerization
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The silver complex (2c)2 AgBF4: 1H NMR (CD2Cl2): δ = 0.87 (m, 24 H), 1.02 (m, 16 H), 1.48 (m, 16 H), 2.39 (m, 8 H), 2.54 (m, 8 H), 7.09 (s, 4 H), 7.14 (s, 4 H), 7.69 (s, 2 H); LDTOF-MS: m/z calcd for C148H164Ag: 2048.19; found: 2049.5.